WO2013013356A1 - Amphiphilic macromolecule and use - Google Patents
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- WO2013013356A1 WO2013013356A1 PCT/CN2011/001578 CN2011001578W WO2013013356A1 WO 2013013356 A1 WO2013013356 A1 WO 2013013356A1 CN 2011001578 W CN2011001578 W CN 2011001578W WO 2013013356 A1 WO2013013356 A1 WO 2013013356A1
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/52—Amides or imides
- C08F220/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
- C08F220/56—Acrylamide; Methacrylamide
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- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B24/00—Use of organic materials as active ingredients for mortars, concrete or artificial stone, e.g. plasticisers
- C04B24/16—Sulfur-containing compounds
- C04B24/161—Macromolecular compounds comprising sulfonate or sulfate groups
- C04B24/163—Macromolecular compounds comprising sulfonate or sulfate groups obtained by reactions only involving carbon-to-carbon unsaturated bonds
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- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B24/00—Use of organic materials as active ingredients for mortars, concrete or artificial stone, e.g. plasticisers
- C04B24/24—Macromolecular compounds
- C04B24/26—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C04B24/2652—Nitrogen containing polymers, e.g. polyacrylamides, polyacrylonitriles
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- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B24/00—Use of organic materials as active ingredients for mortars, concrete or artificial stone, e.g. plasticisers
- C04B24/24—Macromolecular compounds
- C04B24/26—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C04B24/2688—Copolymers containing at least three different monomers
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F226/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
- C08F226/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a single or double bond to nitrogen
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
- C09K8/02—Well-drilling compositions
- C09K8/03—Specific additives for general use in well-drilling compositions
- C09K8/035—Organic additives
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
- C09K8/42—Compositions for cementing, e.g. for cementing casings into boreholes; Compositions for plugging, e.g. for killing wells
- C09K8/46—Compositions for cementing, e.g. for cementing casings into boreholes; Compositions for plugging, e.g. for killing wells containing inorganic binders, e.g. Portland cement
- C09K8/467—Compositions for cementing, e.g. for cementing casings into boreholes; Compositions for plugging, e.g. for killing wells containing inorganic binders, e.g. Portland cement containing additives for specific purposes
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
- C09K8/58—Compositions for enhanced recovery methods for obtaining hydrocarbons, i.e. for improving the mobility of the oil, e.g. displacing fluids
- C09K8/584—Compositions for enhanced recovery methods for obtaining hydrocarbons, i.e. for improving the mobility of the oil, e.g. displacing fluids characterised by the use of specific surfactants
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
- C09K8/60—Compositions for stimulating production by acting on the underground formation
- C09K8/602—Compositions for stimulating production by acting on the underground formation containing surfactants
- C09K8/604—Polymeric surfactants
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
- C09K8/60—Compositions for stimulating production by acting on the underground formation
- C09K8/607—Compositions for stimulating production by acting on the underground formation specially adapted for clay formations
- C09K8/608—Polymer compositions
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
- C09K8/60—Compositions for stimulating production by acting on the underground formation
- C09K8/62—Compositions for forming crevices or fractures
- C09K8/66—Compositions based on water or polar solvents
- C09K8/68—Compositions based on water or polar solvents containing organic compounds
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
- C09K8/60—Compositions for stimulating production by acting on the underground formation
- C09K8/84—Compositions based on water or polar solvents
- C09K8/86—Compositions based on water or polar solvents containing organic compounds
- C09K8/88—Compositions based on water or polar solvents containing organic compounds macromolecular compounds
- C09K8/882—Compositions based on water or polar solvents containing organic compounds macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
- C08F220/283—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety and containing one or more carboxylic moiety in the chain, e.g. acetoacetoxyethyl(meth)acrylate
Definitions
- the invention relates to an amphiphilic polymer and the use thereof, and the amphiphilic polymer is suitable for oil field drilling, cementing, fracturing, crude oil gathering and transportation, sewage treatment, sludge treatment and papermaking, and can be used as an enhanced oil recovery drive.
- the main function of the tertiary oil recovery polymer is to reduce the fluidity ratio, adjust the water absorption profile, and improve the oil recovery profile by increasing the viscosity of the solution and reducing the water phase permeability of the reservoir.
- Solution viscosity and viscosity stability are important indicators for measuring the effect of polymer flooding and are a key issue affecting mining results.
- the comprehensive moisture content of oil fields continues to increase, the difficulty of oilfield exploitation and stable production is increasing, and the requirements for polymers for tertiary oil recovery are also increasing.
- Heavy oil mining is a common problem worldwide. Heavy oil has the characteristics of high viscosity, colloidal asphaltene or high wax content. The heavy oil concentrates about 70% of sulfur and about 90% of nitrogen in crude oil, and the lighter part of heavy oil accounts for about 70% of the total. The part that can be converted by the current technology, but efficient conversion is still difficult; the heavier part, which accounts for about 20% of the total heavy oil, is difficult to convert directly with the existing technology; the heaviest 10% is the heavy oil residue, rich More than 70% of the metals in heavy oil and more than 40% of the sulfur and nitrogen are not effectively converted into light products. Heavy oil is not easy to flow in the formation, wellbore and oil pipelines.
- Heavy oil production methods can be mainly divided into injection fluid extraction (such as hot water flooding, steam stimulation, steam flooding, etc.) and stimulation production methods (such as horizontal wells, composite branch wells, electric heating, etc.).
- Chemical viscosity reducer can effectively disperse and emulsify heavy oil, significantly reduce the viscosity of heavy oil, reduce the flow resistance of heavy oil in the formation and wellbore, which can reduce the energy consumption of mining process, reduce emission pollution, and improve heavy oil recovery. The yield is of great significance.
- the present invention relates to an amphiphilic polymer having repeating units as described below: structural unit A, high sterically hindered structural unit B, and amphiphilic structure for regulating molecular weight, molecular weight distribution, and charge characteristics Unit C.
- the structural unit A which modulates the molecular weight, molecular weight distribution and charge characteristics comprises (meth)acrylamide-based monomer units and/or (meth)acrylic monomer units A 2 ;
- the (meth)acrylamide monomer unit and the (meth)acrylic monomer unit A 2 are included .
- the molecular weight of the amphiphilic polymer can usually be selected as needed, and the use is relatively between 100 and 20 million.
- the (meth)acrylamide monomer unit A has a structure represented by the following formula (1):
- 1 is 11 or a methyl group
- R 2 and R 3 are each independently an alkyl group selected from H and C r C 3
- R 2 and R 3 are preferably H.
- the (meth)acrylic monomer unit A 2 is (meth)acrylic acid and/or (meth)acrylic acid salt; and the methacrylic acid salt is preferably sodium methacrylate.
- the (meth)acrylamide monomer unit A accounts for 70 to 99 mol%, preferably 70 to 90 mol%, more preferably 72.85 to 78 mol%, of all repeating units of the entire amphiphilic polymer. .
- the (meth)acrylic monomer unit A 2 accounts for 1 to 30 mol%, preferably 1 to 25 mol%, more preferably 20 to 25 mol%, based on the total number of repeating units of the entire amphiphilic polymer.
- the structural unit A which functions to adjust the molecular weight, the molecular weight distribution, and the charge characteristic has the formula (2)
- 1 is 11 or methyl;
- R 2 and R 3 are each independently selected from the group consisting of H, C r C 3 alkyl; R 2 and R 3 are preferably H; selected from H or methyl;
- Gr is -OH Or -0"Na + ;
- m and n represent the mole percentage of the structural unit in all repeating units of the entire amphiphilic polymer;
- m is 70-99 mol%, preferably 70-90 mol%, more preferably 72.85-78 mol%
- n is from 1 to 30 mol%, preferably from 1 to 25 mol%; more preferably from 20 to 25 mol%.
- R r R 3 in formula (2) is preferably H, and Gr is preferably -0"Na + .
- the high sterically hindered structural unit B contains at least a structure G; the structure G is an annular hydrocarbon structure formed on the basis of two adjacent carbon atoms of the main chain or is selected from the formula (3) The structure represented; the optional unit B contains the formula (4)
- R6 is selected from the group represented by the following formula (5 (6): CI3 ⁇ 4— 0(CH 2 ) 2 COOCH 2 CH 3
- a is an integer of 1 to 11; preferably 1 to 7;
- R 7 is H or methyl
- R 8 is selected from - HPhOH, -OCH 2 Ph, -OPhOH, -OPhCOOH and salts thereof, -NHC(CH 3 ) 2 CH 2 S0 3 H and salts thereof , -OC(CH 3 ) 2 (CH 2 ) b CH 3 , -NHC(CH 3 ) 2 (CH 2 ) e CH 3 , -OC(CH 3 ) 2 CH 2 C(CH 3 ) 2 (CH 2 ) d CH 3 , - HC(CH 3 ) 2 CH 2 C(CH 3 ) 2 (CH 2 ) e CH 3 ,
- b and c are each an integer of 0-21, preferably 1-11; d and e are each an integer of 0-17, preferably 1-7; f is an integer of 2-8, preferably 2-4; X—is C1—or Br—.
- the high sterically hindered structural unit B contains the structure G and the structure shown in the formula (4).
- the structure G in the above high sterically hindered structural unit B accounts for 0.02 to 2 mol%, preferably 0.02 to 1.0 mol%, more preferably 0.05 to 0.5 mol%, based on the total repeating unit of the entire amphiphilic polymer.
- the structure represented by the formula (4) in the above high sterically hindered structural unit B accounts for 0.05 to 5 mol%, preferably 0.1 to 2.5 mol%, more preferably in the total repeating unit of the entire amphiphilic polymer. 0.1-1.0mol% o
- the high B has the structure shown in the formula (7):
- G is as defined above, and is preferably a structure represented by the formula (3), ; R 7 and R 8 are as defined in the above formula (4;).
- ⁇ and y respectively represent the mole percentage of the structural unit in all repeating units of the entire amphiphilic polymer;
- X is 0.02-2 mol%, preferably 0.02-1.0 mol%, r is more preferably 0.05-0.5 mol%;
- y is 0.05 -5 mol%, preferably 0.1 to 2.5 mol%, more preferably 0.1 to 1.0 mol%.
- R 9 is H or a methyl group
- R 10 is -N + (CH 3 ) 2 (CH 2 CH 3 X-, -N + ((CH 2 ).CH 3 ) 3 X- or - N + (CH 3 )((CH 2 ) T CH 3 ) 2 X;
- ⁇ is an integer from 3 to 21
- ⁇ is an integer from 2 to 9
- ⁇ is an integer from 3 to 15, and
- ⁇ is 3-17, ⁇ is 2-5, and ⁇ is 3-11.
- the above-mentioned amphiphilic structural unit C accounts for 0.05 to 10 mol%, preferably 0.1 to 5.0 mol%, more preferably 0.5 to 1.8 mol%, based on the total number of repeating units of the entire amphiphilic polymer.
- amphiphilic polymer has the structure shown in formula (9):
- R4, m, n are as defined in the above formula (2); R 7 , R 8 , G, x, y are as defined in the formula (7); R 9 , R 1()
- the definition is as shown in the formula (8), and z represents the mole percentage of the structural unit in all the repeating units of the entire amphiphilic polymer, and z is 0.05 to 10 mol%, preferably 0.1 to 5.0 mol%, more preferably 0.5 to 1.8. Mol%.
- the present invention specifically provides the polymer compound represented by the following formulas (I) to (X): ⁇
- the amphiphilic polymer of the present invention has a molecular weight of from 1,000,000 to 20,000,000; preferably from 4 million to 12 million.
- amphiphilic polymer of the present invention can be prepared by a method known in the art, for example, by structural unit monomers, high sterically hindered structural unit monomers and two, which function to adjust molecular weight, molecular weight distribution and charge characteristics.
- the hydrophilic unit monomer is polymerized by an initiator; the polymerization reaction may be a suspension polymerization, an emulsion polymerization, a solution polymerization, a precipitation polymerization, or the like, which is well known in the art.
- a typical preparation method is as follows: Dispersing or dissolving the above monomers in a water system by stirring, and initiating polymerization under nitrogen gas to form an amphiphilic polymer.
- the related art for preparing an amphiphilic polymer in the prior art can be used for the preparation of the amphiphilic polymer of the present invention.
- the monomers used in the preparation of the amphiphilic polymer can be directly obtained commercially or directly prepared according to the prior art to J.
- the synthesis route of some monomers is described in detail in the specific examples.
- Fig. 1 is a graph showing the viscosity-concentration relationship of an amphiphilic polymer prepared in Example 1 of the present invention at 85 ° C in a mineralization degree of 3 X 10 4 mg/L.
- Fig. 2 is a graph showing the viscosity-temperature relationship of the amphiphilic polymer obtained in Example 1 of the present invention in a concentration of 1 750 mg/L in 3 X 10 4 mg/mineralized saline.
- Example 1 The invention is further illustrated by the following specific examples, but the invention is not limited to the following examples.
- Example 1 The invention is further illustrated by the following specific examples, but the invention is not limited to the following examples.
- amphiphilic polymer synthesized in this embodiment is represented by the formula ( ⁇ ):
- the total weight of the total reaction system is added to the reaction vessel at a weight of 1/4 of the total reaction system.
- the molar percentages m, n, x, y, z of each repeating unit are 78%, 20%, and 0.2, respectively. %, 1%, and 0.8% were stirred to completely dissolve them, and a pH adjuster was added thereto to adjust the reaction solution to have a pH of about 10, and the oxygen was removed by nitrogen gas for 30 minutes.
- the initiator was added under nitrogen protection, sealed with nitrogen for 10 min, and then reacted at 25 ° C.
- the reaction was completed for about 6 h, and the reaction was completed.
- the obtained product was dried to obtain a powdery amphiphilic polymer. Molecular weight for the amphiphilic polymer 580x l0 4.
- amphiphilic polymer synthesized in this embodiment is represented by the formula (IX):
- the figure shows that the amphiphilic polymer solutions of Examples 1-5 still have good tackifying ability under high temperature and high salinity conditions.
- the high steric hindrance unit in the amphiphilic polymer reduces the degree of rotational freedom in the main chain, increases the rigidity of the macromolecular chain, makes the macromolecular chain difficult to distort and tends to stretch, resulting in an increase in macromolecular hydrodynamic radius, and
- the amphiphilic structural unit forms an association microdomain by intramolecular or intermolecular interaction, which significantly improves the solution viscosity-increasing ability under high temperature and high salt conditions.
- Test method 25ml of three oilfield electro-de-oil samples were added to a 50ml plugged test tube at a temperature of 25 °C, and 25ml of an aqueous solution of amphiphilic polymers of different concentrations prepared by steaming water was added, and the test tube plug was tightly closed. Use manual mode to shake or place the test tube in the shaker box. Shake it horizontally 80-100 times. The amplitude should be greater than 20cm. After mixing thoroughly, loosen the test tube plug. The viscosity reduction rate of crude oil is calculated according to the following formula:
- Table 1 shows that the amphiphilic polymers of Examples 6-10 have good viscosity reducing effects on the three oil samples. As the concentration of the amphiphilic polymer solution increases, the viscosity reduction rate increases. When the concentration of the solution is the same, the viscosity of the oil sample increases and the corresponding viscosity reduction rate increases. The amphiphilic polymer effectively emulsifies and disperses the crude oil through the synergistic action of the high steric hindrance unit and the amphiphilic structural unit, and the viscosity of the crude oil is remarkably lowered.
- amphiphilic polymer of the present invention for oil field drilling, cementing, fracturing, crude oil gathering, sewage treatment, sludge treatment and papermaking, or as an enhanced oil recovery agent, heavy oil viscosity reducer, Fracturing fluid, clay stabilizer, sewage treatment agent, paper retention aid or reinforcing agent.
- the solution When used as an oil displacing agent, the solution still has a significant viscosity-increasing effect under high temperature and high salt conditions, which can improve the recovery rate of crude oil.
- a heavy oil viscosity reducer by effectively dispersing and emulsifying the heavy oil, the viscosity of the heavy oil is significantly reduced, and the flow resistance of the heavy oil in the formation and the wellbore is reduced.
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NO11870061A NO2738190T3 (en) | 2011-07-26 | 2011-09-16 | |
ES11870061.6T ES2641318T3 (en) | 2011-07-26 | 2011-09-16 | Amphiphilic macromolecule and use |
EA201490340A EA025880B1 (en) | 2011-07-26 | 2011-09-16 | Amphiphilic macromolecule and use thereof |
CA2842705A CA2842705C (en) | 2011-07-26 | 2011-09-16 | Amphiphilic macromolecule and use |
DK11870061.6T DK2738190T3 (en) | 2011-07-26 | 2011-09-16 | Amphiphilic macromolecule and use |
MYPI2014700166A MY173059A (en) | 2011-07-26 | 2011-09-16 | Amphiphilic macromolecule and use |
US14/235,035 US9260555B2 (en) | 2011-07-26 | 2011-09-16 | Amphiphilic macromolecule and the purpose of this amphiphilic macromolecule |
EP11870061.6A EP2738190B1 (en) | 2011-07-26 | 2011-09-16 | Amphiphilic macromolecule and use |
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CN2011102103441A CN102382243B (en) | 2011-07-26 | 2011-07-26 | Amphiphilic polymer and application |
CN201110210344.1 | 2011-07-26 |
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EP (1) | EP2738190B1 (en) |
CN (1) | CN102382243B (en) |
CA (1) | CA2842705C (en) |
DK (1) | DK2738190T3 (en) |
EA (1) | EA025880B1 (en) |
ES (1) | ES2641318T3 (en) |
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Cited By (2)
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US9260555B2 (en) | 2011-07-26 | 2016-02-16 | Beijing Junlun Runzhong Science & Technology Co., Limited | Amphiphilic macromolecule and the purpose of this amphiphilic macromolecule |
US9738741B2 (en) | 2011-07-26 | 2017-08-22 | Beijing Junlun Runzhong Science & Technology Co., Limited | Amphiphilic macromolecule and use thereof |
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CN103570864B (en) * | 2012-07-27 | 2016-05-25 | 中国石油化工股份有限公司 | A kind of acrylamide terpolymer and its preparation method and application |
CN105646777A (en) * | 2015-12-29 | 2016-06-08 | 四川光亚聚合物化工有限公司 | Hydrophobic associated polymer and preparation method thereof |
CN106701053A (en) * | 2016-12-08 | 2017-05-24 | 北京百特泰科能源工程技术有限公司 | High-polymer crude oil activator, and preparation method and application thereof |
CN108794680B (en) * | 2018-06-30 | 2020-09-15 | 胜利油田盛嘉化工有限责任公司 | Preparation method of thickened oil viscosity reducer |
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- 2011-07-26 CN CN2011102103441A patent/CN102382243B/en active Active
- 2011-09-16 EP EP11870061.6A patent/EP2738190B1/en active Active
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Publication number | Priority date | Publication date | Assignee | Title |
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US9260555B2 (en) | 2011-07-26 | 2016-02-16 | Beijing Junlun Runzhong Science & Technology Co., Limited | Amphiphilic macromolecule and the purpose of this amphiphilic macromolecule |
US9738741B2 (en) | 2011-07-26 | 2017-08-22 | Beijing Junlun Runzhong Science & Technology Co., Limited | Amphiphilic macromolecule and use thereof |
Also Published As
Publication number | Publication date |
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EP2738190A4 (en) | 2015-08-19 |
NO2738190T3 (en) | 2018-01-06 |
US9260555B2 (en) | 2016-02-16 |
EA025880B1 (en) | 2017-02-28 |
EA201490340A1 (en) | 2014-05-30 |
CN102382243B (en) | 2013-03-27 |
CA2842705C (en) | 2016-07-05 |
CN102382243A (en) | 2012-03-21 |
MY173059A (en) | 2019-12-23 |
CA2842705A1 (en) | 2013-01-31 |
ES2641318T3 (en) | 2017-11-08 |
US20150183911A1 (en) | 2015-07-02 |
DK2738190T3 (en) | 2017-10-02 |
EP2738190A1 (en) | 2014-06-04 |
EP2738190B1 (en) | 2017-08-09 |
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